4-Hydroxybenzaldehyde → 4-[2-(1,3-Dioxan-2-yl)ethoxy]benzaldehyde

HRID 783

Reaktionsgleichung

Reaktionsgleichung von HRID 783
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.Br[CH2:11][CH2:12][CH:13]1[O:18][CH2:17][CH2:16][CH2:15][O:14]1.[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C.C(#N)C>[O:14]1[CH2:15][CH2:16][CH2:17][O:18][CH:13]1[CH2:12][CH2:11][O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1

Komponenten

7

Edukt 4

HCID 1264-HydroxybenzaldehydeHCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 5206561,3-Dioxane, 2-(2-bromoethyl)-

Produkt 1

HCID 196934674-[2-(1,3-Dioxan-2-yl)ethoxy]benzaldehydeAusbeute 100,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

In a 500 ml flask, 120 ml of acetonitrile, 13.8 g of 4-hydroxybenzaldehyde, 21.1 g of 2-(2-bromoethyl)-1,3-dioxane, 1.8 g of potassium iodide, and 35.8 g of potassium carbonate were placed and then, reacted at 80° C. for 5 hrs. Thereafter, 200 ml of ethyl acetate was added to the reaction mixture and washed once with a saturated aqueous potassium carbonate solution, distilled water, and saturated saline. The washed organic phase was dried over anhydrous magnesium sulfate and removed solvent, to give 25.6 g of 4-(2-[1,3]-dioxane-2-yl-ethoxy)benzaldehyde.

Aufarbeitung

  1. customreacted at 80° C. for 5 hrs
  2. washwashed once with a saturated aqueous potassium carbonate solution
  3. distillationdistilled water, and saturated saline
  4. dry with materialThe washed organic phase was dried over anhydrous magnesium sulfate
  5. customremoved solvent

Quellen und Nachweise

ORD-Eintrag
ord-d6f09b988e0848769dd846f380d71108
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05723258

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